The Journal. - The Fall of Kimberly Guilfoyle

Episode Date: October 14, 2026

After the White House asked her to step down, Kimberly Guilfoyle resigned from her position as the U.S. Ambassador to Greece. A Wall Street Journal investigation laid out a series of text messages in which Guilfoyle asked a conservative supporter for a payment of $100,000 to her American Express account. WSJ’s Dana Mattioli reports on the messages that led to Guilfoyle’s fall. Imani Moise hosts. Further Listening: Jared Kushner’s Albania Headache: Flamingos, Contested Land and Cocaine  Kristi Noem’s $200 Million Mistake Sign up for WSJ’s free What’s News newsletter. Learn more about your ad choices. Visit megaphone.fm/adchoices

Yesterday, Kimberly Gilfoyle resigned from her post as U.S. ambassador to Greece, and it was because of a Wall Street Journal investigation. During Gilfoyle's ambassadorship, the Wall Street Journal looked into allegations that she was using her position for personal gain. After that investigation was published, the journal received information about a series of text messages. Can you just give us a sense of how many text messages landed on your desk? Probably more than 100. That's our colleague, Dana Madioli.

Also, we received emails, and by the end of this, my colleagues and I had gone through hundreds, hundreds, more than a year's worth of text messages between the person who sent us the text messages and the then ambassador to Greece. In multiple texts, Gilfoyle talks about a potential payment of $100,000 to her American Express account. Honey, please, I need you to get this done for me today with a prayer hand emoji. What was your initial reaction to getting this tranche of text messages? You know, the text messages got sent to myself and my three other colleagues, and they were really just eye-opening. They were very graphic text messages.

And the first thing we said about doing was authenticating them, right? The texts were between Gilfoyle and a man named Eric Dieters. Ultimately, Deeters didn't make the payment telling Gilfoyle that it would cost him his marriage. Later, Deeters provided the messages to Dana, and Dana got to work verifying that the texts were real. So what we did was myself and my colleague Rebecca Ballhouse got on a Google Meet, a video phone call with Eric Deeters. And we had him pull up his cell phone to the text messages with Kimberly Guilfoil. In the meet, Deeter's clicked on the contact card and showed the report. that the phone number he had been texting was the same cell as the one they knew to be Kimberly

Gilfoyles. And then he very slowly scrolled through every single text message with her for over a year, and we read them to match what was sent to us with what was actually on his phone, and to see the context in between the things that he didn't send us, of course, right? We were able to see over a year's worth of text messages to help authenticate these messages for our publication, which obviously we have very high standards before we publish anything. Through a lawyer, Gilfuel disputed the authenticity of the messages in the reporting, but declined to provide specifics. Through these text messages, what Dana and her colleagues were able to see

was that Eric Dieters and Kimberly Gilfoyle had an arrangement, where he would pay her money, and Gilfoyle would promise Deer's access to some of the most powerful people in the Trump administration. They were sort of both using each other in some ways. And when you read the text messages back and forth, you could see how much these two people seemed to need. each other. Welcome to The Journal, our show about money, business, and power. I'm Imani Moise. It's Wednesday, October 14th. Coming up on the show, the Wall Street Journal investigation

that led to Kimberly Guilfoyle's resignation. Eric Dieter said his dealings with Kimberly Gilfoyle began during the early days of COVID. Deeters had launched a MAGA event called Freedom Fest. It was this festival in Kentucky in response to COVID-19 medical mandates. And in order to really get a lot of attention for this festival, Dieter sought to find someone closely aligned with the MAGA movement that could appear as a speaker. And he found Kimberly Gilfoyle during that period and started communicating with her.

And she had a big enough megaphone that she would be a good ambassador for this festival. At the time, Gilfoyle was engaged to Donald Trump Jr. And was a rising MAGA icon herself. She was a former Fox News host, the kind of spokesperson that Dieters was looking for. For her three speaking appearances, Deeters paid Gilfoyle a lot of money. He had given her $300,000 over the space of a few years to appear at his Freedom Fest festival. So now I want to get into a little bit more color about Eric Dieter's.

Can you tell us a little bit about his background? Yeah, so Deeters is a pretty colorful character. He's 63 years old. He was an attorney, and he had a family business with his father where they had some gas stations. But he was also a lawyer. He's also had other pursuits. Deeters co-owned a restaurant chain called Snappy Tomato Pizza. He also had unsuccessful bids for Congress and governor of Kentucky.

He was a morning radio host in Ohio, and he was very closely aligned with the Trump administration. He says he's Trump today, Trump tomorrow, Trump forever. As a lawyer, Dieter's had a reputation, as the courtroom bulls, Bulldog in Ohio. And he got a lot of attention. He's someone who is a, you know, speaks very loudly and could be very impassioned when he speaks to you. And, you know, I think some of that's gotten him some attention from the court system in 2020. He was banned from entering a courthouse in Ohio's Hamilton County after threatening on social media to burn it down. The Kentucky Bar Association twice suspended him, citing aggressive litigation strategies, false statements in court proceedings,

and filing frivolous claims. So this is someone with a, you know, a past of his own. Deeters told the journal he retired as a lawyer. Regarding his run-ins with the court system, he said, quote, these rules that are written by big law to hurt people like me, screw them. After Freedom Fest, Gilfoyle and Deiders began to spend more time together, and he started offering to pay Gilfoyle for more than speaking engagements. As Dana discovered inside his text messages,

Deeters came to Gilfoyle with two big requests. One is this tax write-off that he took that was being investigated by the IRS. Deeters told the journal that he wanted Guilfoyle's help to solve a personal tax issue and get the attention of the IRS chief. The other issue he wanted help with involved an extradition request. Deeters was advising victims of an Ohio surgeon who had fled the country after allegations of malpractice. So when you speak to Deeters, the thing he gets most impassioned about is the work he's doing for these victims of this doctor who fled to Pakistan. And he's working with hundreds of former patients of this doctor who are

suing the doctor for alleged medical malpractice, negligence, and fraud. In a lawsuit filed against Dieters, the doctor's malpractice insurer MedPro group accused Deeters of a, quote, calculated scheme to extract payments from the insurer. Deeters denied the accusations in an interview, calling it, quote, the most ridiculous BS lawsuit of all time. The text showed Deeters asking Gilfoyle for help getting the Justice Department to launch an investigation into the doctor and bring him back to the U.S. soil. He also talked about plans to publicize the case. He wanted to get his story of the victims onto Tucker Carlson, which is a conservative media figure. And he said if she did that, he would pay her $1 million.

A million dollars for help landing an appearance on Tucker Carlson. At this point, Dana could see in the text that Gilfoyle was reassuring Deiders that she was doing everything she could for him. She really is trying to help him. She's giving him status updates of all the people she's trying to help him with his tax issue, all the people she's reaching out to around Tucker Carlson to get him on there. And one text message, she even says, no one is working as hard for you than I am, and that I might as well be your personal public relations. She basically says that she's never worked so hard in her life for anything other than what she's trying to do for him. During the months that Dieter's and Gilfoyle were texting

back and forth, Gilfoyle's political career was about to reach another level. In December of 2024, President Trump nominated Gilfoyle to serve as ambassador to Greece. You know, when any ambassador is confirmed, they take a close look at your financial situation, because if you're someone who's in serious debt, you could maybe be swayed by foreign actors to do certain things. That could make you a liability. So that is something that's very closely explored in all of these Senate confirmation hearings. At the same time, Deter's was getting impatient waiting for Gilfoyle to deliver on his request. And as her confirmation hearing neared,

Guilfoyle was becoming increasingly concerned that her text with Deter's were becoming a liability. He starts openly referencing this financial arrangement they have, including with people outside of her. So people like her producer of her podcast, and then she starts getting angry and worrying that he's leaving a damning paper trail that could really hurt her Senate confirmation hearing for her role. as ambassador. She writes to him, it's unbelievable when we have a private arrangement with you that you would now see see a producer talking about money. She got very concerned about Dieter's

being indiscriminate and putting anything about their financial arrangement in writing. This was something that really seemed to stress her out. At a certain point, she says, you're going to cost me my ambassadorship. She's very worried that he keeps referencing the payments to her, their financial, arrangement. She says things like, Eric, I really wish you would stop papering all these things. It's really dangerous and not helpful to you or me while you could simply just call me on Signal. And Signal's an encrypted chat app where things disappear and things are not traceable, right? So she does not want anything in writing, but he keeps putting stuff in writing. In another text, she says, what a nightmare you'll literally cost me my ambassadorship,

stop writing. The communication with Dieter's doesn't stop there. Eventually, Gilfuel would ask him for a payment to her amics account, which would cost her her ambassadorship. That's next. In August of 2020, Gilfoyle was one of the key speakers at the Republican National Convention, where she gave a memorable sign-off. Leaders and fighters for Freedom Act to come! In the four years between the two Trump administrations, Gilfoyle tried to parlay her status as a mega-celebrity into several businesses. There were hair care and fragrance products, a political consulting firm, and a med spa. What we learned is that a lot of the things that she tried to launch barely got off the ground

and were later shuttered. So for instance, in 2022, she launched something called American Dream, which she described as an upscale vodka and champagne brand. And she was seeking $2 million at the time. According to the pitch deck, which is actually really interesting, it's not a normal Wall Street pitch deck or a San Francisco pitch deck. It has all. all of these, like, glamorous shots of her in full-length gowns. It's, like, very flashy. The pitch deck projected that American Dream vodka would reach $75 million in revenue within three years. Guilfoil later dissolved the company.

So that's one instance. She also tried to launch a perfume called Floor de Maga, which really didn't get off the ground, right? So there were a bunch of things like that that just really it was trial and error and most of them did not launch. Do you have any reporting on what President Trump's? thought about Gilfoyle's mega-inspired businesses. So we report that during this period between Trump's first and second terms, he grew frustrated with Gilfoyle because she was soliciting investments from Marilago members for her companies.

You know, at one point he complained that Gilfoyle was supposed to be raising money for him, but instead was at his club fundraising for herself. Then, in 2024, Gilfoyle's engagement with Donald Trump Jr. ended. According to financial disclosures after the split, she had more than a million dollars in liabilities, including a boat loan and a mortgage. For her hopes to become ambassador to Greece, that debt could be a problem. And as her confirmation hearing approached, Gilfoyle complained to friends that she was broke, according to people that we spoke with.

Just days before her confirmation hearing in July 2025, Gilfoyle reached out to Deiders with a pressing request. Can you read us some of the text messages that she starts sending to Deeters at this time? So the same week of her confirmation hearing is the most splashy text, I think we see. So in July 3rd, over Signal, she sends him a PDF to an American Express wiring instructions. And it says, you could just send it here. It won't show up anywhere if you wire money to American Express. That's all that will show, please. And that was a pretty telling text.

Eric also told us she came up with the cover before the confirmation saying, you know, let's create a story. that you owe me money from a long time ago. And she asked him to put in a letter that he owes her $100,000. In another message, Gilfoyle tells Deiders, I will be your Trump ride or die. There's another text where she says, honey, please, I need you to get this done for me today. And she had a prayer hands emoji,

and then it had the PDF with the bill payment instructions for American Express. And like I said, this was just a few days before her July 9th confirmation hearing. How did Deiders respond to that request for $100,000? He considered it at first, but then he ultimately decided he couldn't do it because he felt like she wasn't really getting what he needed done. He also said it could have affected his marriage. Why did he say that this $100,000 was going to be a deal breaker this time? I think for him he just felt like she was just using him to get more money. And that, you know, the $300,000 he had already paid hadn't gotten him.

any favors with the White House, and he was very skeptical about shelling out another $100,000 if it didn't seem like any of the promises she was making were to actually happen. I think he wanted to have the action before he paid her. So he wrote to her, I have paid you $300,000 over the years. As of this memo, I have not received one favor. I am not naive or a sucker. I need results. Again, gilfoil axed eaters to stop creating a paper trail and to call her on signal instead.

In the fall of 2025, Gilfoyle's ambassadorship was confirmed. She spent a year in Greece. Publicly, her priority was trying to persuade European countries to pay a premium for American gas. Around this time, the journal started looking into how Gilfoyle was misusing her position at the embassy for personal gain. And then last week, it all came to a head when Dana and the team published their investigation

about her texts with Dieters. The day before the story came out, The reporting team called Secretary of State Marco Rubio for comment. Rubio was on a flight to Athens. After he landed in Greece, a reporter asked if he was going to do anything in response to the journal's findings. We don't conduct these things on a press conference on a tarmac in a foreign country because you wrote a story or somebody else wrote a story

because some source gave it to you. So get that out of your head because that's never the way it's going to work with me. In the days after the Wall Street Journal's investigation came out, Gilfoyle contacted the White House and said the text messages between her and Dieter's were AI generated. According to people familiar with the matter, officials didn't believe her claims. Yesterday, on her very first day as White House press secretary, Katie Zachariah had an announcement. We have asked Ambassador Guilfoyle to resign. She has been a wonderful asset to the team, and we wish her well. According to people familiar with the matter, Trump didn't speak directly

to Guilfoyle before making the decision. Later that day, Gilfell resigned via social media post. A lawyer for Gilfoyle said that she had been paid to speak at events before her nomination and was owed a balance for traveling and supporting those events. Why is this such a big deal? I think it's a big deal because, you know, these ambassadors are sent overseas to represent U.S. interests abroad, right? They're supposed to develop these relationships and promote U.S. business, and it's supposed to be this, like, virtuous cycle. And from what we were able to report about the ambassador's time in Greece is there were other things happening that did not fall under the remand of an ambassador.

And we've had a number of politicians come out and say that they will be investigating this conduct. Over the years and multiple terms, we have kind of seen this narrative of interesting relationships with foreign business leaders take place with different officials within the Trump administration. what was the line that Kimberly Guilfoyle crossed? Why is this case getting so much attention? I think partly it's getting so much attention because of how Bladen it was. We have all these text messages and emails showing exactly how the sausage is made.

I think that part of why this is getting so much attention is because of really how solid the reporting is. That's all for today. Wednesday, October 14th. The journal is a co-production of Spotify and the Wall Street Journal. If you like our show, follow us on Spotify or wherever you get your podcasts. We're out every weekday afternoon. Thanks for listening. See you tomorrow.